Defining the Criminal Class: A Case Study of Sentences Delivered by Judge Henry Gildersleeve and Recorder Frederick Smyth


Did New York City judges have a hand in constructing the criminal class? Answering this question requires a careful examination of who the judges were, which political, social, or personal biases may have influenced their decisions, and who may have borne the brunt of their discrimination. A comparison of sentencing data for Judge Henry Gildersleeve and Recorder Frederick Smyth, both of whom tried thousands of criminal cases in the latter half of the nineteenth century, yields two useful observations: first, the sentences the judges delivered for the same crimes varied considerably on a case-by-case basis, indicating that the defendants’ physical appearance, social class, ethnicity, political affiliation, age, and criminal record may all have affected the punishment they received. [1] Second, the evidence suggests that Judge Gildersleeve tended to punish thieves and recidivists with particular severity. He repeatedly imprisoned robbers, burglars, and pickpockets for the same non-violent offenses. Their removal from society relegated these men and women to the rank and file of the state’s prison system. In his capacity as judge, Gildersleeve actively shaped the definition of New York City’s criminal class.

Criminal Courthouse, New York City
Postcard depicting a criminal courthouse on White Street in Lower Manhattan, ca. 1910.


Inconsistent Sentencing

This sampling of criminal sentences echoes trends that have been observed by legal historians for decades. “Just as in the case with other opinions of individuals, judicial opinions necessarily represent in a measure the personal impulses of the judge…and these impulses are determined by the judge’s lifelong series of previous experiences”. [2] Charles Haines, who spent his life studying the development of the United States’ judicial system, made this assertion as he compared the discharges issued by New York City judges in 1915. [3] The findings of his study reveal considerable discrepancies in the number of discharges granted by each judge, with some justices dismissing over 70 percent of cases and others less than 7 percent. [4] Tables 1.1 and 1.2 illustrate a similar inconsistency in nineteenth century punishments: Smyth’s maximum sentence for burglary was 5 years, while Gildersleeve sentenced one burglar to 10 years in prison. [5]

A comparison of burglary sentences delivered by Judge Gildersleeve and Recorder Smyth.


Gildersleeve Punishes Property Crimes

Gildersleeve was known for his contempt for crimes against property and his intolerance of pickpockets in particular. [6] On January 24, 1880 he sentenced a defendant to 5 years in prison for robbery and assault. [7] The amount stolen was $3.70. On the same day, Smyth sentenced another man to one year in prison for robbery and assault, this time for a theft amounting to $1.70. [8] The two dollar difference in the amount stolen is hardly sufficient to explain why one thief was imprisoned for five times as long as the other.

Gildersleeve’s disdain for violations of personal property meant that defendants who came before him were more likely to receive lengthier sentences for larceny, burglary, and robbery than they may have received at the hands of a different judge. On January 18, 1877, Gildersleeve presided over the trial of two men indicted for selling adulterated milk. [9] He found both men guilty and fined them $25 and $50 each. The same day, Gildersleeve found John Brocks guilty of stealing $40 from his roommate. For this offense, he sentenced Brocks to four years in state prison. [10] Apparently, the judge saw thieves as imminent threats to the public welfare who needed to be locked away. Businessmen who tampered with food staples, on the other hand, were less dangerous and could be satisfactorily disciplined with a fine. The difference in punishment for these crimes could indicate a more widespread shift towards protection of capitalist business interests, but it could also point to Gildersleeve’s personal beliefs about which individuals constituted the criminal class. [11]

Moreover, many of Gildersleeve’s sentences appeared to be influenced by the judge’s opinion of the defendant. In January, 1886, he presided over the trial of Mr. Tip Little, an elderly burglar who pled guilty to artificially raising the value of a check from $4 to $806.[12] Tip appealed to Gildersleeve for mercy, citing his old age and good character in an attempt to avoid the maximum sentence. His argument struck a chord with the Judge, who shortened his prison term to five years. Almost as an afterthought, the article describing Tip’s plea notes that his partner in crime, a black man named Isaac Cooper, was sent to prison for seven and a half years. Cooper, like Tip, had pled guilty to passing the phony check; but, unlike Tip, he did not benefit from Gildersleeve’s mercy. [13] Whether the difference in their punishments stemmed from racial bias, or bias based on age and social class is impossible to determine. What is clear is that Gildersleeve did not pass sentences based solely on the crime in question. He observed the defendants’ appearance, listened to their pleas, and formulated the punishment he deemed just.

Photo of a 19th century gang of pickpockets.
Photo of a 19th century gang of pickpockets.


Smyth Condemns Violent Crime

Recorder Smyth, like Gildersleeve, was fairly intolerant of crimes against property. The average sentences given by both judges for grand larceny and burglary differ by just two months. (See Tables 1.1, 1.2, 2.1, and 2.2 below). Smyth was quick to sentence one woman to two and a half years in prison for stealing a pocketbook, and sentenced a notorious burglar to a five year term for breaking and entering. [14]

Sentencing data for Judge Gildersleeve and Recorder Smyth. Average sentence for burglary: Smyth – 2 years 11 months; Gildersleeve – 2 years 9 months.


KK. 18
Sentencing data for Judge Gildersleeve and Recorder Smyth. Average sentence for grand larceny: Smyth – 2 years 11 months; Gildersleeve – 2 years 9 months.


However, Smyth appeared more inclined to crack down on violent crimes. In 1880 he declared that “he was determined to do all he could to put a stop to the practice of carrying pistols” and that any defendants who came before him, regardless of the charges against them, would be given the maximum sentence if they were found to have a pistol in their possession. [15] Smyth made good on his promise, sending John Bray to prison for two and a half years for attempted burglary once he discovered that Bray had been carrying a firearm. [16]

“Justice” for Recidivists

Smyth and Gildersleeve diverge more significantly in their treatment of recidivists. Repeat offenders convicted by Smyth for burglary and grand larceny received sentences that averaged three months longer than those given to first-time offenders. Gildersleeve, on the other hand, sentenced recidivists to prison terms that averaged six months longer than those of first time offenders for burglary, and eight months longer for grand larceny. Apparently, the more times an individual appeared before the court, the longer their next sentence would be.

Vincent Van Gogh. "Prisoners Exercising (After Doré". Van Gogh painted this is 1890 during his self-imposed exile to the insane asylum at Saint-Rémy. It is a copy of Doré's painting "Newgate: The Exercise Yard". Newgate was a prison in nineteenth century London and served as a model for New York City's Sing Sing.
Vincent Van Gogh. “Prisoners Exercising (After Doré”. Van Gogh painted this is 1890 during his self-imposed exile to the insane asylum at Saint-Rémy. It is a copy of Doré’s painting “Newgate: The Exercise Yard”. Newgate was a prison in nineteenth century London and served as a model for New York City’s Sing Sing. [17]
In 1884, two young men were found guilty of assaulting a broker and stealing his watch. Both pled guilty, and one was sentenced to three years in prison. Upon discovering that the other man had already been to prison twice and had also served a term in the penitentiary, Gildersleeve sent him “back to the old place” for five years – a sentence almost twice as long as that of his partner, a first-time offender. [18] In another instance, Gildersleeve took pity on a young father convicted of stealing a gold watch. [19] Taking into account the man’s youth and his lack of a criminal record, Gildersleeve sent him to the Elmira Reformatory instead of state prison. [20]

Gildersleeve’s decisions in these cases suggest that he defined the criminal class according to a set of specific biases. He tended to send repeat offenders to prison for longer terms than their novice counterparts. The overwhelming majority of these individuals were convicted for property crimes. In the sample of 105 prisoners sentenced by Gildersleeve between 1876 and 1889, only 14 were serving time for violent offenses. [21] The remaining 87% of convicts were imprisoned for various forms of theft, fraud, and felonious mischief. [22] Gildersleeve’s propensity to punish recidivists for property crimes at a higher rate than other classes of offenders suggests that these individuals embodied his definition of the criminal type. He funneled them into the state’s prisons, thereby removing them from their communities and families for extended periods of time. Upon returning from prison, the newly freed often had difficulty finding employment because of their unsavory record. If they were unable to work, some would turn to theft and violence in order to survive. When they were caught engaging in these crimes of desperation, they came to court once more and the cycle began again.

Pickpocket George Appo’s account of his struggle to reform demonstrates the hopelessness many ex-cons felt after emerging from years behind bars:“My time expired [5 April 1896] and I was roaming about the city in search of some honest employment… [A]fter about six weeks of search, I gave it up and through necessity, I began to drift back to my former crooked life.” [23]

Historian Timothy Gilfoyle, in his analysis of Appo’s experience with New York City’s criminal justice system, explains that nineteenth century criminals were at a huge disadvantage upon their release from prison. [24] Before 1878, state assistance for ex-convicts was non-existent. The only agency offering financial aid to ex-cons was the privately-funded Prison Association, which by one account spent less than $2,000 annually to assist former inmates. In 1878, a state official was appointed to offer financial assistance and employment advice to prisoners approaching the end of their terms. However, between 1886 and 1893 this agent only provided aid for 61% of New York’s discharged criminals, amounting to an average of nine dollars per person. [25]

Men loitering in an alley off of Mulberry Street known as "Bandit's Roost". These men typify the slum-dwellers who often resorted to thievery for lack of a better way to support themselves and their families.
Men loitering in an alley off of Mulberry Street known as “Bandit’s Roost”. These men typify the slum-dwellers who often resorted to thievery for lack of a better way to support themselves and their families.


Conclusion: The “Criminal Class”

Given these dismal prospects, it is hardly surprising that many released convicts returned to a life of crime. Gildersleeve’s tendency to treat repeat offenders with particular severity can only have exacerbated the problem. Bias against “hardened criminals” would have resulted in the continuous imprisonment of the same types of offenders. The cycle of punishment and re-incarceration could easily have become self-perpetuating. Gildersleeve and his fellow judges, by deciding to sentence repeat offenders for longer terms, helped determine who was being sent to prison and, consequently, who came to constitute the criminal class.

Did these criminals threaten the public welfare because of an inherently evil nature, or were they victims of a faulty justice system? The data presented here and the analysis of the judiciary’s role in the nineteenth century support the latter explanation. Gildersleeve and Smyth were free to administer disparate punishments for the same crime and were able to discriminate against repeat offenders, perpetuating a cycle of re-incarceration that trapped 3,500-4,000 people behind bars each year. [26] For the better part of the late nineteenth century, the biased decisions of a few powerful men shaped the definition of New York City’s criminal class.


[1] This comparison is based on a sampling of sentences recorded in the Sing Sing inmate registers for the years 1876-1894.

[2] Haines, Charles Grove. “General Observations on the Effects of Personal, Political, and Economic Decisions of Judges”. (Illinois Law Review vol. 17, no. 2, 1922): 99.

[3] Ibid., 105.

[4] Ibid.

[5] These are the maximum sentences in this sample. Smyth may have punished burglary more harshly in cases not documented in our data.

[6] Gilfoyle, Timothy. A Pickpocket’s Tale. (New York: W.W. Norton & Company, 2006), 71.

[7] “The Perils of the Street At Night,” New York Herald (New York, New York), January 24, 1880: 9.

[8] Ibid. Smyth’s leniency in this case may be attributed to the shaky evidence presented by the complainant, who was intoxicated at the time the robbery took place. However, the difference between this sentence and Gildersleeve’s is large enough to be worth noting.

[9] “Court Notes,” New York Times (New York, New York), January 19, 1877.

[10] Ibid.

[11] Gilfoyle, 71.

[12] “Tip Little’s Plea For Mercy,” New York Times (New York, New York), January 16, 1886.

[13] Ibid.

[14] “Summary of Law Cases,” New York Herald (New York, New York), February 4, 1880: 2

[15] “Recorder Smyth on Carrying Pistols,” New York Tribune (New York, New York), January 27 1880:

[16] Ibid.


[18] “Gone Back to the Old Place,” New York Times (New York, New York), September 17, 1884: 8

[19] “A Young Husband Sentenced,” New York Times (New York, New York), January 26, 1883.

[20] Ibid.


[22] Ibid.

[23] Gilfoyle, 276.

[24] Ibid., 307.

[25] Ibid.

[26] Ibid., 100. Also of interest: “Between 1870 and 1900, the state’s daily prison population – the nation’s largest – fluctuated between 2,526 and 3,614.”